Estate Supervisor / Head Caretaker Location: Oxshott, Surrey Salary: Circa £45,000 Hours: Monday to Friday, (30Hr Week average) Own vehicle required Are you an experienced facilities or site professional with strong handyman skills and a proactive approach to estate upkeep? We are recruiting on behalf of a prestigious private estate in Oxshott for a hands-on Estate Supervisor / Head Caretaker to oversee maintenance, contractor activity, and resident liaison across two high-end residential estates (one primary, one smaller). Key Responsibilities: * Conduct regular patrols and inspections of roads, verges, signage, and gates * Carry out pre-condition surveys before building work begins on indivual properties, documenting the condition of estate roads/verges before site work begins and ensuring contractors make good any damage caused. * Monitor compliance with estate by-laws (e.g., vehicle limits, working hours) * Liaise with site agents and contractors to ensure rules are followed and damages are repaired * Oversee external contractors (e.g., landscapers, gate engineers, sweepers, etc.) * Maintain and clean communal features including gates (washing and occasional painting), street signage, and verges * Remove fly-tipped items, storm debris, and fallen branches (or liaise with tree surgeons if necessary) * Review and report CCTV footage to the Estate Manager to identify any breaches * Act as a point of contact for residents regarding estate issues and incidents * Submit weekly updates and photographic reports to the Managing Agents * Ensure unauthorised visitors or vehicles are monitored and addressed Ideal Candidate: * Strong facilities or estate/ site management background * Comfortable managing contractors and resolving issues independently * Strong hands-on maintenance and handyman skills * Organised, observant, and proactive with good attention to detail * IT literate – able to email updates and photographic reports * Strong communicator who can liaise effectively with both residents and contractors * Able to cover occasional weekend incidents remotely if required * Candidate must have their own vehicle to travel between areas and transport tools or handle tasks like fly-tipping removal. ⚙️ Additional Info: * Role spans two neighbouring estates; the secondary site requires similar duties but is smaller in scope * Estate guidelines are strict and must be consistently enforced to preserve resident quiet enjoyment * This is a highly valued position offering long-term stability for the right person * Self-employed welcome